The specific objectives of the proposed research are to effect the total synthesis of the aglycone of venturicidin and the natural material malyngolide. These compounds are of interest because of their demonstrated antibiotic activities. In a more general sense the investigation will provide methods and concepts of broader generality for application to other areas of organic synthesis. The syntheses address questions regarding kinetic resolution, inherent symmetry properties and operations, spirodienolate anions, and intramolecular metal ion binding by covalently attached crown ethers in an enzyme-mimicking fashion. The concept of symmetrical extension of functionality, if general, would prove useful in applications to the synthesis of the acyclic backbone of even more complex ansamycin antibiotics.